NPASS Compound

Structure

NPC69914 OpenBabel07101718312D 39 41 0 0 0 0 0 0 0 0999 V2000 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 3 1 0 0 0 0 2 4 2 0 0 0 0 3 6 1 0 0 0 0 4 9 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 29 1 0 0 0 0 18 24 2 0 0 0 0 18 27 1 0 0 0 0 19 25 2 0 0 0 0 19 28 1 0 0 0 0 20 26 2 0 0 0 0 20 30 1 0 0 0 0 21 34 1 0 0 0 0 22 35 1 0 0 0 0 23 36 1 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 37 2 0 0 0 0 28 38 2 0 0 0 0 29 39 1 0 0 0 0 30 39 2 0 0 0 0 31 34 2 0 0 0 0 31 37 1 0 0 0 0 32 35 2 0 0 0 0 32 38 1 0 0 0 0 33 36 2 0 0 0 0 33 39 1 0 0 0 0 M CHG 1 39 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	524.4
Volume:	610.85
LogP:	7.449
LogD:	4.754
LogS:	-1.808
# Rotatable Bonds:	21
TPSA:	29.66
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.079
Synthetic Accessibility Score:	2.995
Fsp3:	0.472
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.302
MDCK Permeability:	3.1552754080621526e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.063
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	97.37139129638672%
Volume Distribution (VD):	3.544
Pgp-substrate:	0.6526904702186584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.16
CYP1A2-substrate:	0.324
CYP2C19-inhibitor:	0.557
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.076
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.998
CYP2D6-substrate:	0.206
CYP3A4-inhibitor:	0.929
CYP3A4-substrate:	0.767

ADMET: Excretion

Clearance (CL):	4.776
Half-life (T1/2):	0.864

ADMET: Toxicity

hERG Blockers:	0.928
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.008
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.219
Skin Sensitization:	0.988
Carcinogencity:	0.049
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.961

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC69914

Natural Product ID:	NPC69914
*Common Name:**	Niphatoxin C
IUPAC Name:	1-[(Z)-12-pyridin-3-yldodec-5-enyl]-3-[(Z)-9-pyridin-3-ylnon-2-enyl]pyridin-1-ium
Synonyms:	Niphatoxin C
Standard InCHIKey:	QMKWJZIROZRKOP-JXSNUWOOSA-N
Standard InCHI:	InChI=1S/C36H50N3/c1(3-6-10-14-21-34-24-18-27-37-31-34)2-4-9-13-17-29-39-30-20-26-36(33-39)23-16-12-8-5-7-11-15-22-35-25-19-28-38-32-35/h2,4,12,16,18-20,24-28,30-33H,1,3,5-11,13-15,17,21-23,29H2/q+1/b4-2-,16-12-
SMILES:	C(/C=CCCCC[n+]1cccc(C/C=CCCCCCCc2cccnc2)c1)CCCCCc1cccnc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251665
PubChem CID:	24763331
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0001764] Pyridinium derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	red sea	n.a.	PMID[12762806]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18027906]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22469701]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	collected by hand at a depth of 10 m off the shore of Iriomote Island, Okinawa Prefecture, Japan	2009-JUN	PMID[23855338]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24948562]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[27015002]
NPO33070	Callyspongia sp.	Species	n.a.	n.a.	n.a.	New Guinea	n.a.	PMID[8158156]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	5

Activity Type	# Activity
Cell Line	5
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2654	Individual Protein	P2X purinoceptor 7	Homo sapiens	Activity	=	41.0	%	PMID[468259]
NPT1970	Cell Line	THP-1	Homo sapiens	Activity	=	0.0	%	PMID[468259]
NPT1970	Cell Line	THP-1	Homo sapiens	Activity	=	99.0	%	PMID[468259]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	11500.0	nM	PMID[468259]
NPT1970	Cell Line	THP-1	Homo sapiens	Activity	=	101.0	%	PMID[468259]
NPT1970	Cell Line	THP-1	Homo sapiens	Activity	=	185.0	%	PMID[468259]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC69914 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	1026
0.1-0.2	10489
0.2-0.3	19734
0.3-0.4	6436
0.4-0.5	2525
0.5-0.6	1784
0.6-0.7	532
0.7-0.8	148
0.8-0.85	15
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC476131
0.9512	High Similarity	NPC476322
0.904	High Similarity	NPC329825
0.8943	High Similarity	NPC240136
0.8943	High Similarity	NPC471402
0.8943	High Similarity	NPC297486
0.8571	High Similarity	NPC91958
0.8527	High Similarity	NPC290094
0.8397	Intermediate Similarity	NPC146373
0.8397	Intermediate Similarity	NPC245244
0.8397	Intermediate Similarity	NPC166424
0.8333	Intermediate Similarity	NPC202957
0.8333	Intermediate Similarity	NPC169625
0.8281	Intermediate Similarity	NPC143603
0.8261	Intermediate Similarity	NPC314102
0.8261	Intermediate Similarity	NPC251722
0.8231	Intermediate Similarity	NPC265605
0.8231	Intermediate Similarity	NPC182570
0.8231	Intermediate Similarity	NPC48564
0.8226	Intermediate Similarity	NPC27802
0.8209	Intermediate Similarity	NPC89490
0.8148	Intermediate Similarity	NPC329896
0.8148	Intermediate Similarity	NPC475105
0.8148	Intermediate Similarity	NPC475090
0.8138	Intermediate Similarity	NPC40070
0.8029	Intermediate Similarity	NPC101165
0.8	Intermediate Similarity	NPC471313
0.8	Intermediate Similarity	NPC471311
0.7984	Intermediate Similarity	NPC76540
0.797	Intermediate Similarity	NPC46358
0.7959	Intermediate Similarity	NPC470233
0.791	Intermediate Similarity	NPC27740
0.7887	Intermediate Similarity	NPC316811
0.7887	Intermediate Similarity	NPC315348
0.7887	Intermediate Similarity	NPC32002
0.7862	Intermediate Similarity	NPC86288
0.7826	Intermediate Similarity	NPC282398
0.7812	Intermediate Similarity	NPC235843
0.777	Intermediate Similarity	NPC471322
0.777	Intermediate Similarity	NPC256893
0.7746	Intermediate Similarity	NPC150259
0.7692	Intermediate Similarity	NPC169433
0.7642	Intermediate Similarity	NPC83987
0.7635	Intermediate Similarity	NPC477974
0.7603	Intermediate Similarity	NPC20144
0.7576	Intermediate Similarity	NPC476566
0.755	Intermediate Similarity	NPC138842
0.7534	Intermediate Similarity	NPC469766
0.7532	Intermediate Similarity	NPC201634
0.7518	Intermediate Similarity	NPC324611
0.7517	Intermediate Similarity	NPC470111
0.75	Intermediate Similarity	NPC471312
0.75	Intermediate Similarity	NPC280852
0.7466	Intermediate Similarity	NPC469779
0.7466	Intermediate Similarity	NPC469761
0.7466	Intermediate Similarity	NPC469784
0.7466	Intermediate Similarity	NPC469780
0.7466	Intermediate Similarity	NPC469767
0.7466	Intermediate Similarity	NPC469768
0.7466	Intermediate Similarity	NPC469783
0.7463	Intermediate Similarity	NPC162689
0.7463	Intermediate Similarity	NPC54102
0.745	Intermediate Similarity	NPC63545
0.7436	Intermediate Similarity	NPC476446
0.7436	Intermediate Similarity	NPC478182
0.7436	Intermediate Similarity	NPC469813
0.7436	Intermediate Similarity	NPC78375
0.7434	Intermediate Similarity	NPC325903
0.7422	Intermediate Similarity	NPC231655
0.7403	Intermediate Similarity	NPC167635
0.7403	Intermediate Similarity	NPC193740
0.74	Intermediate Similarity	NPC201380
0.74	Intermediate Similarity	NPC469811
0.74	Intermediate Similarity	NPC179787
0.7397	Intermediate Similarity	NPC73767
0.7388	Intermediate Similarity	NPC81561
0.7379	Intermediate Similarity	NPC65408
0.7372	Intermediate Similarity	NPC124542
0.7372	Intermediate Similarity	NPC59779
0.7372	Intermediate Similarity	NPC471177
0.7365	Intermediate Similarity	NPC477977
0.7355	Intermediate Similarity	NPC293487
0.7351	Intermediate Similarity	NPC321911
0.7342	Intermediate Similarity	NPC56233
0.7333	Intermediate Similarity	NPC288838
0.7329	Intermediate Similarity	NPC297034
0.7313	Intermediate Similarity	NPC148140
0.731	Intermediate Similarity	NPC96102
0.7303	Intermediate Similarity	NPC53947
0.729	Intermediate Similarity	NPC129721
0.729	Intermediate Similarity	NPC216643
0.7286	Intermediate Similarity	NPC135488
0.7279	Intermediate Similarity	NPC88097
0.7279	Intermediate Similarity	NPC110126
0.7279	Intermediate Similarity	NPC104483
0.7278	Intermediate Similarity	NPC471178
0.7273	Intermediate Similarity	NPC476219
0.7266	Intermediate Similarity	NPC122718
0.726	Intermediate Similarity	NPC105127
0.726	Intermediate Similarity	NPC84911
0.7244	Intermediate Similarity	NPC477591
0.7244	Intermediate Similarity	NPC56765
0.7233	Intermediate Similarity	NPC478183
0.7215	Intermediate Similarity	NPC478184
0.7215	Intermediate Similarity	NPC97367
0.7215	Intermediate Similarity	NPC317105
0.72	Intermediate Similarity	NPC471323
0.7197	Intermediate Similarity	NPC229173
0.7197	Intermediate Similarity	NPC215584
0.7197	Intermediate Similarity	NPC44773
0.7192	Intermediate Similarity	NPC29886
0.7192	Intermediate Similarity	NPC261195
0.7181	Intermediate Similarity	NPC476454
0.7179	Intermediate Similarity	NPC469897
0.7178	Intermediate Similarity	NPC150048
0.7178	Intermediate Similarity	NPC203754
0.7153	Intermediate Similarity	NPC82295
0.7152	Intermediate Similarity	NPC478185
0.7152	Intermediate Similarity	NPC470203
0.7143	Intermediate Similarity	NPC116961
0.7134	Intermediate Similarity	NPC221786
0.7134	Intermediate Similarity	NPC474880
0.7117	Intermediate Similarity	NPC471579
0.7115	Intermediate Similarity	NPC51054
0.7115	Intermediate Similarity	NPC476464
0.7114	Intermediate Similarity	NPC279081
0.7113	Intermediate Similarity	NPC212125
0.7101	Intermediate Similarity	NPC215519
0.7089	Intermediate Similarity	NPC470204
0.7089	Intermediate Similarity	NPC255229
0.7089	Intermediate Similarity	NPC122141
0.7089	Intermediate Similarity	NPC81229
0.7083	Intermediate Similarity	NPC315320
0.7078	Intermediate Similarity	NPC24678
0.7078	Intermediate Similarity	NPC105818
0.707	Intermediate Similarity	NPC236711
0.7063	Intermediate Similarity	NPC477975
0.7059	Intermediate Similarity	NPC21605
0.7051	Intermediate Similarity	NPC212376
0.7051	Intermediate Similarity	NPC75540
0.7051	Intermediate Similarity	NPC70922
0.7051	Intermediate Similarity	NPC211572
0.7051	Intermediate Similarity	NPC80597
0.7044	Intermediate Similarity	NPC71079
0.7044	Intermediate Similarity	NPC225018
0.7039	Intermediate Similarity	NPC314372
0.7037	Intermediate Similarity	NPC32534
0.7037	Intermediate Similarity	NPC91895
0.7037	Intermediate Similarity	NPC474897
0.7025	Intermediate Similarity	NPC135141
0.7025	Intermediate Similarity	NPC318065
0.7025	Intermediate Similarity	NPC206819
0.7025	Intermediate Similarity	NPC92796
0.702	Intermediate Similarity	NPC190296
0.7019	Intermediate Similarity	NPC98187
0.7007	Intermediate Similarity	NPC198988
0.7	Intermediate Similarity	NPC59084
0.7	Intermediate Similarity	NPC90723
0.7	Intermediate Similarity	NPC474217
0.7	Intermediate Similarity	NPC2949
0.7	Intermediate Similarity	NPC230002
0.6993	Remote Similarity	NPC143872
0.6993	Remote Similarity	NPC306397
0.6987	Remote Similarity	NPC469786
0.6987	Remote Similarity	NPC259644
0.6987	Remote Similarity	NPC73952
0.6987	Remote Similarity	NPC469765
0.6987	Remote Similarity	NPC25008
0.6987	Remote Similarity	NPC469763
0.6987	Remote Similarity	NPC469760
0.6985	Remote Similarity	NPC84268
0.6963	Remote Similarity	NPC473901
0.6962	Remote Similarity	NPC286427
0.6954	Remote Similarity	NPC63157
0.6954	Remote Similarity	NPC473868
0.6943	Remote Similarity	NPC476297
0.6937	Remote Similarity	NPC194881
0.6928	Remote Similarity	NPC159856
0.6928	Remote Similarity	NPC469525
0.6928	Remote Similarity	NPC157583
0.6928	Remote Similarity	NPC285731
0.6918	Remote Similarity	NPC475990
0.6918	Remote Similarity	NPC41257
0.6914	Remote Similarity	NPC278366
0.6914	Remote Similarity	NPC127730
0.6899	Remote Similarity	NPC469785
0.689	Remote Similarity	NPC82331
0.6879	Remote Similarity	NPC200214
0.6875	Remote Similarity	NPC165370
0.6871	Remote Similarity	NPC322488
0.6855	Remote Similarity	NPC469762
0.6852	Remote Similarity	NPC195507
0.6852	Remote Similarity	NPC85918
0.6852	Remote Similarity	NPC2165
0.6852	Remote Similarity	NPC274229
0.6846	Remote Similarity	NPC29702
0.6846	Remote Similarity	NPC325252
0.6839	Remote Similarity	NPC471957
0.6828	Remote Similarity	NPC471589
0.6826	Remote Similarity	NPC237188

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC69914 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	466
0.1-0.2	781
0.2-0.3	1127
0.3-0.4	2241
0.4-0.5	2419
0.5-0.6	1527
0.6-0.7	466
0.7-0.8	106
0.8-0.85	14
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8582	High Similarity	NPD3944	Approved
0.8582	High Similarity	NPD3942	Approved
0.855	High Similarity	NPD2118	Approved
0.855	High Similarity	NPD2119	Approved
0.8387	Intermediate Similarity	NPD4823	Approved
0.8387	Intermediate Similarity	NPD4824	Approved
0.8358	Intermediate Similarity	NPD3475	Approved
0.8358	Intermediate Similarity	NPD3476	Approved
0.8252	Intermediate Similarity	NPD4547	Phase 3
0.8235	Intermediate Similarity	NPD1994	Approved
0.8235	Intermediate Similarity	NPD1995	Approved
0.8235	Intermediate Similarity	NPD1993	Approved
0.8231	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD268	Approved
0.8231	Intermediate Similarity	NPD271	Approved
0.8222	Intermediate Similarity	NPD715	Phase 3
0.8182	Intermediate Similarity	NPD7469	Discontinued
0.8175	Intermediate Similarity	NPD4029	Approved
0.8175	Intermediate Similarity	NPD4030	Approved
0.8175	Intermediate Similarity	NPD4028	Approved
0.8134	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD991	Phase 2
0.8	Intermediate Similarity	NPD1598	Discontinued
0.7987	Intermediate Similarity	NPD6497	Approved
0.7933	Intermediate Similarity	NPD5418	Discontinued
0.7926	Intermediate Similarity	NPD9583	Approved
0.7907	Intermediate Similarity	NPD269	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD2837	Discontinued
0.7887	Intermediate Similarity	NPD2072	Approved
0.7887	Intermediate Similarity	NPD2073	Approved
0.7887	Intermediate Similarity	NPD2069	Approved
0.7887	Intermediate Similarity	NPD2075	Approved
0.7887	Intermediate Similarity	NPD2074	Approved
0.7887	Intermediate Similarity	NPD2071	Approved
0.7887	Intermediate Similarity	NPD2070	Approved
0.7887	Intermediate Similarity	NPD2068	Approved
0.7857	Intermediate Similarity	NPD2141	Approved
0.7857	Intermediate Similarity	NPD2140	Approved
0.7857	Intermediate Similarity	NPD2142	Approved
0.7801	Intermediate Similarity	NPD792	Discontinued
0.7793	Intermediate Similarity	NPD3813	Approved
0.7786	Intermediate Similarity	NPD3385	Approved
0.7778	Intermediate Similarity	NPD9357	Approved
0.777	Intermediate Similarity	NPD2466	Phase 3
0.777	Intermediate Similarity	NPD2465	Approved
0.777	Intermediate Similarity	NPD2462	Phase 3
0.7761	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD4510	Discontinued
0.7724	Intermediate Similarity	NPD2006	Phase 2
0.7692	Intermediate Similarity	NPD2896	Discontinued
0.7647	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD768	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD1627	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2430	Phase 2
0.7568	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7111	Discontinued
0.7551	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD3339	Approved
0.7534	Intermediate Similarity	NPD1722	Approved
0.7517	Intermediate Similarity	NPD1270	Approved
0.7517	Intermediate Similarity	NPD4703	Approved
0.7517	Intermediate Similarity	NPD4702	Approved
0.7516	Intermediate Similarity	NPD7287	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6554	Approved
0.75	Intermediate Similarity	NPD45	Approved
0.7484	Intermediate Similarity	NPD7216	Approved
0.7484	Intermediate Similarity	NPD6771	Discontinued
0.7484	Intermediate Similarity	NPD7217	Approved
0.7484	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3262	Approved
0.7483	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5255	Approved
0.7432	Intermediate Similarity	NPD1988	Phase 1
0.7422	Intermediate Similarity	NPD9099	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD9098	Phase 3
0.7391	Intermediate Similarity	NPD6471	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD9396	Approved
0.7388	Intermediate Similarity	NPD9392	Approved
0.7379	Intermediate Similarity	NPD200	Phase 2
0.7379	Intermediate Similarity	NPD201	Phase 2
0.7376	Intermediate Similarity	NPD3654	Approved
0.7372	Intermediate Similarity	NPD4384	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD5315	Discontinued
0.7368	Intermediate Similarity	NPD4641	Discontinued
0.7365	Intermediate Similarity	NPD3717	Discontinued
0.7365	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1395	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1649	Discontinued
0.7342	Intermediate Similarity	NPD6446	Discontinued
0.7329	Intermediate Similarity	NPD1380	Discovery
0.731	Intermediate Similarity	NPD1256	Approved
0.731	Intermediate Similarity	NPD1255	Approved
0.731	Intermediate Similarity	NPD1254	Approved
0.731	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1253	Approved
0.7296	Intermediate Similarity	NPD5862	Discovery
0.7285	Intermediate Similarity	NPD2110	Approved
0.7284	Intermediate Similarity	NPD2751	Phase 1
0.7279	Intermediate Similarity	NPD786	Approved
0.7278	Intermediate Similarity	NPD2720	Phase 1
0.7278	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD976	Approved
0.7273	Intermediate Similarity	NPD977	Approved
0.7273	Intermediate Similarity	NPD975	Approved
0.7273	Intermediate Similarity	NPD803	Phase 1
0.7261	Intermediate Similarity	NPD8026	Phase 1
0.7237	Intermediate Similarity	NPD3100	Discontinued
0.7233	Intermediate Similarity	NPD3929	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3323	Discontinued
0.7212	Intermediate Similarity	NPD8408	Discontinued
0.7208	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3409	Phase 1
0.7195	Intermediate Similarity	NPD3341	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1383	Phase 3
0.7181	Intermediate Similarity	NPD1382	Phase 2
0.7179	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2582	Approved
0.7179	Intermediate Similarity	NPD2581	Approved
0.7171	Intermediate Similarity	NPD1661	Suspended
0.7161	Intermediate Similarity	NPD2809	Approved
0.7161	Intermediate Similarity	NPD2165	Phase 1
0.7152	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4973	Approved
0.7133	Intermediate Similarity	NPD1427	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1183	Approved
0.7115	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3113	Approved
0.7115	Intermediate Similarity	NPD3114	Approved
0.7115	Intermediate Similarity	NPD3115	Approved
0.7115	Intermediate Similarity	NPD3112	Approved
0.7113	Intermediate Similarity	NPD9284	Approved
0.7099	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2511	Approved
0.7086	Intermediate Similarity	NPD3401	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5671	Approved
0.7083	Intermediate Similarity	NPD9206	Approved
0.7083	Intermediate Similarity	NPD9207	Approved
0.7081	Intermediate Similarity	NPD2333	Discontinued
0.7073	Intermediate Similarity	NPD2406	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6044	Discontinued
0.707	Intermediate Similarity	NPD1192	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5300	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD9598	Discontinued
0.7047	Intermediate Similarity	NPD945	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4804	Approved
0.7044	Intermediate Similarity	NPD5400	Approved
0.7034	Intermediate Similarity	NPD9726	Discontinued
0.7019	Intermediate Similarity	NPD5636	Discontinued
0.7014	Intermediate Similarity	NPD947	Approved
0.7013	Intermediate Similarity	NPD5538	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD272	Approved
0.7006	Intermediate Similarity	NPD2580	Discontinued
0.7006	Intermediate Similarity	NPD6026	Approved
0.7	Intermediate Similarity	NPD5787	Discontinued
0.6993	Remote Similarity	NPD1683	Approved
0.6993	Remote Similarity	NPD9080	Approved
0.6987	Remote Similarity	NPD1917	Discontinued
0.6978	Remote Similarity	NPD4811	Discontinued
0.6974	Remote Similarity	NPD4509	Discontinued
0.6974	Remote Similarity	NPD751	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2771	Approved
0.697	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2172	Phase 1
0.6962	Remote Similarity	NPD4326	Phase 2
0.6959	Remote Similarity	NPD206	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5020	Approved
0.6954	Remote Similarity	NPD4805	Approved
0.6951	Remote Similarity	NPD5324	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2089	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1328	Approved
0.6943	Remote Similarity	NPD2061	Approved
0.6933	Remote Similarity	NPD5436	Phase 1
0.6933	Remote Similarity	NPD4024	Phase 3
0.6928	Remote Similarity	NPD8122	Approved
0.6928	Remote Similarity	NPD1032	Phase 2
0.6928	Remote Similarity	NPD8123	Approved
0.6923	Remote Similarity	NPD7564	Discontinued
0.6918	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5065	Approved
0.6909	Remote Similarity	NPD3859	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4047	Discontinued
0.6905	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8020	Approved
0.6901	Remote Similarity	NPD8021	Approved
0.6894	Remote Similarity	NPD3583	Phase 2
0.6894	Remote Similarity	NPD6635	Approved
0.6894	Remote Similarity	NPD8129	Discovery
0.689	Remote Similarity	NPD3610	Approved
0.689	Remote Similarity	NPD3609	Approved
0.6887	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5555	Phase 1

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data